New method of obtaining of known (E)-2-cyano-3-alkoxy-2-butenoates 1 are going to be presented. These esters are very useful to synthesis of isoxazole and pyrazole derivatives [2], from which there are many biologically active compounds [1]. So, they are very essentially valuable compounds in organic synthesis but so far methods of their obtaining were not yielded (about 40%) [3,4] or very hazardous diazomethane was used to synthesize them [5].

The way of the synthesis of 2-cyano-3-alkoxy-2-butenoates 1,developed by us, as a result of reaction of appropriate cyanoacetates with orthoacetates in the tertiary amine presence, is the new efficient method giving practically quantitative yield of these valuable semi-products [6].

References:

1. S. Ryng, M.Zimecki, A.Fedorowicz, A. Jezierska: Reactions of 5-amino-3-methylisoxazole-4-carboxylic acid hydrazide with carbonyl compounds: immunological activity and QSAR studies of products. Archiv der Pharmazie,2001;334: 71-78.

2. H. Baba, I. Hori, T.Hayashi, H. Midorikawa : Reactions of α-Cyano-β-methoxy-β-alkylacrylic Esters with Hydrazine and Hydroxylamine. Bulletin of the Chemical Society of Japan 1969; 42: 1653-1659.

3. A. Haller: Preparation des ethers β-alcoyloxy-αcyanocrotoniques isomeres des ethers acetoalcoylcyanacetiques. Comptes Rendus 1900;130:1221-1225.

4. Y. Urushibara: The identity of the two possible isomeric methyl ethyl β-methyl-α,γ-dicyanoglutaconates. Bulletin of the Chemical Society of Japan 1928;3: 261-265.

5. T. Hayashi, I. Hori, H. Baba, H. Midorikawa: Studies on Geometric Isomerism by Nuclear Magnetic Resonance. Stereochemistry of α-Cyano-β-alkoxy-β-alkylacrylic esters. Journal of Organic Chemistry 1965,30:695–699.

6. Andrzej Regiec, Paweł Gadziński: Nowe sposoby wytwarzania estrów kwasów 2-cyjano-3-alkoksy-2-butenianowych, zgłoszenie patentowe (patent application) nr P.397558, 2011

• Legal notice:
  

  Copyright (c) Pielaszek Research, all rights reserved.
  The above materials, including auxiliary resources, are subject to Publisher's copyright and the Author(s) intellectual rights. Without limiting Author(s) rights under respective Copyright Transfer Agreement, no part of the above documents may be reproduced without the express written permission of Pielaszek Research, the Publisher. Express permission from the Author(s) is required to use the above materials for academic purposes, such as lectures or scientific presentations.
  In every case, proper references including Author(s) name(s) and URL of this webpage: https://science24.com/paper/25498 must be provided.

1. Synthesis and cytotoxic activity of new Pt (II) complexes with nitropyrazoles in aerobic and hypoxic conditions
2. Research into transformations of 5-amino-3-methyl- 4-isoxazolecarboxylic acid hydrazide under orthoesters influence
3. Electrochemical studies of Pt (II) complexes with potential bioreductive properties